The Battle of Long Island by Daniel P. Murphy, Ph.D.

The Battle of Long Island was the first major battle fought by George Washington and the Continental army. It revealed that both had a lot to learn about waging war against competently led professionals. It set in motion a series of military reverses that threatened the survival of Washington's army and the revolutionary cause.

Rout on Long Island

On August 22, General Howe began landing troops on Long Island. Over the next three days, he concentrated a force of 20,000 men there. Washington immediately reinforced his own troops entrenched above Brooklyn, bringing the number of Americans stationed on Long Island to 10,000. Washington suffered from very poor intelligence about British movements. He believed that Howe's landing on Long Island was a feint made with fewer than 10,000 troops.

Nathanael Greene, the American commander on Long Island, was incapacitated by illness. Washington replaced him first with John Sullivan, then with Israel Putnam, a senior major general. Putnam was a brave Patriot, but he had no knowledge of the topography of Long Island, and like his commander underestimated the capabilities of British regulars. Putnam sent 4,000 men from the fortifications on Brooklyn Heights forward to the Heights of Guano, a rugged, wooded ridge. These men, commanded by John Sullivan on the left and William Alexander, Lord Stirling, on the right, were to guard the roads leading to Brooklyn. The troops in this exposed position were too few to hold it effectively. Because of the rough terrain, communication was difficult and units were isolated from each other. Washington inspected and approved Putnam's disposition of his troops on the evening of August 26. Already the British were setting in motion a devastating attack.

Why did Howe take so long to attack the Americans?

It took a long time for Howe to rest and refit his troops after their long sea voyage. Some had been aboard ship for 125 days before they reached New York. Many were suffering from fevers, scurvy, and the harrowing mental strain of being cooped up in a ship's hold for months.

Howe spent his first few days on Long Island reconnoitering the American lines. He adopted a plan suggested by Henry Clinton. On the night of August 26, Howe led a column of 10,000 men on a march around the American left flank along the Jamaica Road. The only Americans guarding the road were a party of five men, who were quickly surprised and taken prisoner. While Howe made his flanking march, other British troops advanced toward the Americans at the Heights of Guano, keeping them occupied and looking forward.

By nine o'clock on the morning of August 27, Howe was behind the American line and ready to launch his attack. Two guns signaled a general assault. Sullivan's men on the left were swiftly overrun by British forces, which advanced all around them. The Americans turned and ran, pursued by bayonet-wielding redcoats and Hessians. General Sullivan and many others were captured. Lord Stirling held out heroically for a time before his command, too, was crushed. He was taken prisoner, but many of his surviving men found shelter in a swamp. Washington watched Lord Stirling's last stand from a distance and cried out, “Good God! What brave fellows I must this day lose!” More than 1,000 Americans were lost in the rout. The British suffered 392 casualties.

The Retreat from Long Island

After routing the American forward line, Howe did not press on to Brooklyn Heights. Instead, he began preparations for traditional siege operations against the American strongpoint. He justified this lack of aggressiveness by arguing that an assault was not worth the lives lost since he would be able to take the place “at a very cheap rate by regular approaches.” Perhaps Howe was mindful of his experiences at Breed's Hill, and the damage that untrained but desperate Americans could inflict on regulars.

New York was a major American city with 25,000 inhabitants. Only Philadelphia was larger, with a population of 28,000. Boston was significantly smaller with 16,000 people, and Newport, Rhode Island, had 11,000 people. The largest southern city was Charleston with a population of 12,000.

Washington's first thought after the battle was to very imprudently reinforce Brooklyn Heights. As soon as the British navy bestirred itself, his men would be cut off. Fortunately for the Americans, a storm blew in, preventing warships from sailing up the East River. By the evening of August 28, Washington realized that his position on Long Island was untenable. He began gathering boats and called upon John Glover's regiment of fishermen from Marblehead, Massachusetts, to man them. Washington personally supervised the evacuation that began at dusk on August 29. A heavy fog helped conceal the American retreat from the British. By seven o'clock the next morning, Washington's men and all their equipment had been carried over to New York City.